


Fornication Plea!

by DRHPaints



Category: Actor RPF, American (US) Actor RPF, Bill Hader - Fandom, Bill Hader RPF, Conan O'Brien - Fandom, Conan O'Brien RPF, Late Night Host RPF, US Comedians RPF
Genre: Anal Fingering, Anal Sex, Blow Jobs, Cunnilingus, Dom/sub Undertones, Double Penetration, Double Vaginal Penetration, Explicit Language, Explicit Sexual Content, F/M, Face-Fucking, Friends to Lovers, Humor, M/M, Masturbation, Multi, Phone Sex, Plot What Plot/Porn Without Plot, Rimming, Smut, Threesome, Threesome - F/M/M, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2021-02-20
Updated: 2021-02-20
Packaged: 2021-03-16 20:54:26
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,881
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29581950
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: After Bill agrees to be on his friend Anne's web series to review a video game, they admit their long-held attraction to one another. When she brings up the topic of threesomes, Bill mentions a recent discussion with his buddy, Conan O'Brien, and they all meet at Conan's house the next day for some fun.
Relationships: Bill Hader/Conan O'Brien/Original Character(s), Bill Hader/Original Female Character(s)/Conan O'Brien
Comments: 2
Kudos: 10





	Fornication Plea!

**Author's Note:**

  * For [LadyLicquorice](https://archiveofourown.org/users/LadyLicquorice/gifts).



Knocking, Bill hurriedly adjusted the hem of his navy hoodie and smoothed a large hand over his chestnut hair, fingers rattling atop his thick thigh as he heard shuffling from inside.

“Oh hey Bill!” Arms wide and face beaming, Anne joined Bill for a lingering embrace, humming as his powerful arms squeezed. 

“Hey Anne, how’s it going?” Indulging herself, Anne tucked into the curve of Bill’s pale neck, reminded of his delectable scent before she finally admitted that standing in her doorway clinging to his broad body for much longer might garner suspicion.

“Good, good. How’re you? Come on in.” Anne stepped aside, smiling at how Bill toed off his white sneakers before following her through to the living room. 

Bill’s cobalt gaze tracked Anne’s switching hips, big hand in his pockets and eyes averted when they reached the couch and she turned around. “I’m good, thanks. So...we’re playing a game today?”

“Yeah, thanks so much for agreeing to do this. You want anything to drink? A snack before we start?”

Brandishing his water bottle, Bill shook his head. “Nope, I’m alright. Thanks though.”

“Cool. Just give me a couple of minutes and we’ll be ready to go.”

Observing as Anne fiddled with her camera and fired up the XBox, Bill told himself to breathe, to relax. And yet, he tapped the denim of his jeans incessantly, relegating his stare to the ceiling whenever Anne bent over to wiggle a cord into place and unavoidably put her ample cleavage on full display.

On the drive over, Bill tried to convince himself not to be anxious. He knew Anne since their time at the New York Film Academy after all, and with an extensive, deep friendship spanning a multitude of years and topics, Bill shouldn’t need to fret.

But, even back then when they were both involved in other relationships, their harmless flirtation caused Bill to tense up whether he wanted to or not. Now, both single, when Anne asked if he would come along for an afternoon of video games to help her film a review for her web series, though Bill politely accepted, he downplayed his excitement at the thought of the two spending hours together. In her house. Alone. Bill’s mind whirred with possibilities.

“Okay…” Plopping down next to him on the cushion with a grin, Bill reminded himself of the rolling camera and tore his azure eyes away from Anne’s voluptuous body. “All good. Here you go.”

Anne passed Bill a controller, tingling at the sight of his huge hands encompassing the plastic. “Cool, so, you said we’re playing ‘Hitman’?”

“Yeah…” Rolling her eyes, Anne sighed. “Hitman 3. A little obvious I know, but...I figured it might be good for a few laughs.”

Bill’s signature giggle, a high squeak decorated with his squinty left eye and dazzling crooked smile, peeped out, and Anne shivered. “I’m up for it. Though…” Clicking away, Bill flubbed his pink lips as they started to play. “It’s going to become painfully obvious in about two seconds that I don’t know how to kill people properly.”

“What’s the good of watching all that true crime then?” Anne smirked at the screen as they proceeded through the level, all too aware of the pressure of Bill’s shapely thigh against her own.

“I mean...it could come in handy…” Unaware of his alluring pout as he tried to focus on his character, Bill violently mashed the buttons. “You never know when you’re going to need to hide a body. Right?”

Distracted by Bill’s flexing forearms and furrowed brow, Anne didn’t notice she died until Bill pointed at the screen. “So…?”

“Right, right…” Shaking her head to clear away the lustful fog, Anne resumed, but the thoughts of what lurked beneath Bill’s hoodie remained. “So, no offense Bill, but in  _ Barry _ I’ve noticed you never hide a body. Never wear gloves. Why is that?”

“I’m just fucking lazy.” Bill giggled and folded over on himself, shaking his head. “It’s easier to write a bad hitman than a good one, I guess.”

Laughing, Anne advanced to the next area and peeked apprehensively at Bill from the corner of her green eyes. “That’s fair. I’ve also heard you mention it bothers you that people suddenly find you sexy now that you’re playing a murderer.”

“Yeah…” Lower lip stretching and dark brows high, Bill hissed in a breath. “I don’t get it. But multiple people have told me they didn’t think I was attractive until they saw me holding a gun.”

“Oh, I don’t think it’s the gun…” Anne’s fingers raced and she kept her gaze glued to the television. “I think it’s that while you’re shooting you just look so...angry. And you...yell. A lot. As Barry.”

Tittering glee quaking his broad shoulders, Bill licked his pink lips and folded them under. “Still problematic. I’d rather people didn’t think that was appealing.”

“Then stop looking so hot when you kill people, Bill.” Dispatching someone in the game 

herself, Anne didn’t notice Bill’s expressive eyebrow arching in her direction.

After playing a few rounds, during which Anne teased Bill for his inability to navigate and Bill sweetly roasted himself for incompetence, they recorded her intro before deciding to head out for an early dinner.

“So…” Anne accepted her iced tea from the waitress while Bill got a seltzer. “You don’t spend much time gaming, then, I gathered, based on today?”

“Nope.” Chuckling, Bill sipped. “That obvious?”

Nodding, Anne perused the menu. “Yeah, but no big deal. I enjoy it, but some aspects of the gig get a little...tedious.”

“Oh yeah? Like what?”

“Well…” Anne sighed, looking up and blinking. “Like the conventions, for instance. Don’t love going to those. Especially…” Slumping forward, Anne scoffed. “The last Comic Con...I don’t know how…But my sponsor convinced me to cosplay as Lara Croft for ‘promotional purposes’.” Making air quotes, Anne rolled her eyes. “Not great walking around there dressed like that, to be honest.”

“Oh I can imagine…” Bill tried to avoid doing just that as his sapphire eyes trailed over Anne’s enticing figure. “That must be...annoying.”

Hitching up a shoulder, Anne tossed her scarlet mane back and teetered her head. “Yeah, well...it wasn’t the best. But I did--” 

Anne hesitated, and Bill saw a secret little smirk bloom over her plump lips, accompanied by a flush of fuschia. “Oh well, it’s...probably better not to mention that…”

“What?” Leaning in conspiratorially, Bill felt like two teenagers sharing gossip before the waitress interrupted to take their order and he dipped in toward Anne once more. “So...what happened at Comic Con?”

“Well, I…” Biting her lip, Anne looked at Bill apprehensively before exhaling audibly. “Alright...well, so I had this stupid costume on, right? And I met these two guys who do a really cool podcast about PC games. Anyway, so, I’ve been listening to them for years, and we’ve even done a little correspondence on Twitter and such about different games here and there. But I had no idea they were so…” Eyes wide, Anne shook her head as she lost herself in reverie. “Fucking hot.”

Prominent brow inching up his high forehead, Bill smirked. “Oh yeah? Both of them?”

“Mmm...yeah.” Anne didn’t catch how her ecstatic hum caused every dark hair on Bill’s carved forearm to stand alert. “Both. That’s...well….” Chuckling, Anne tucked her chin down demurely and shifted in her seat. “So...you know how those conventions are. The themed rooms and the free drinks… One thing led to another and… we all ended up back in the same room, so…”

Bill trapped a breath in his solid chest, head bobbing as he swallowed. “Oh really? That’s...that’s...yeah…”

Laughing and oblivious to Bill’s squirming, Anne clutched her stomach. “Yeah, and one of them, right at a very inopportune moment, if you catch my drift, thought it appropriate to call out ‘Lara!’ instead of my name.”

“Pfft!” Cloaking his blush with a large hand, Bill descended into giggles. “No he didn’t! That’s terrible!”

“Oh, it was alright…” Anne speared a bite of chicken and shrugged. “I mean...I slept through my first panel the next day and couldn’t walk straight for the rest of Con. I can’t really complain.”

Sauce dripping mindlessly from his forkful of pasta, Bill stared at Anne with deep blue eyes spinning scenario after scenario before eventually blinking himself back to reality. “Oh right. Yeah, that’s...I’ve never done anything like that, so…”

“Really?” Holding a palm in front of her mouth to hide her chewing, Anne’s ginger brows gathered incredulously. “You’ve never had a threeway? But you’re so sexy. How is that possible? Shouldn’t you have, like, a dozen hotties swarming you at all times?”

A squeak of flattered amusement left Bill’s pink lips and he lifted a vast shoulder. “Nope. Never. But…” Prodding his food while he contemplated, Bill’s sculpted jawline flickered nervously and he resolutely studied the tablecloth. “It’s funny you mention that. I was just talking about threesomes with a buddy of mine the other day. He’s never had one either and I think most people would be surprised.”

“Oh yeah?” Nudging with an elbow, Anne scooted a little closer to Bill in the booth, excited to hear the juicy detail. “Who is it?”

Cobalt eyes darting around, Bill lowered his flinty voice. “Conan.”

Anne gasped and smiled. “What? How? I…” Shaking her head, Anne tossed up a hand in dismay. “Another tall handsome comedy man! And you two aren’t out here getting it on the regular? What the hell? Everyone should be climbing that jolly ginger giant!”

As Bill chuckled, he realized they inadvertently sat pressed against each other. “Yeah, I was shocked. So…” Food forgotten, Bill rested his weight forward, fingers atwitter on his thick thighs and licking his lips. “You think Conan is sexy?”

Magnetized by Bill’s reserved manner, his uneven smile, the perfect pinpricks of silver-etched stubble gracing his chiseled features; Anne’s voice sank into a sultry valley and she leaned in. “Yeah...I do…” Anne allowed herself to brush up against Bill’s firm arm as she nodded. “Do you? Think he’s hot?”

Bobbing his head, Bill couldn’t believe how close Anne’s face floated. So close… “Yeah, I, I do…” The cords of Bill’s neck stood out with effort before his gaze skidded away. “But I don’t know if he’s...into that. Really. We were just kind of being silly about it. You know…”

“Oh…” Anne took a risk, reaching up to clear the silken feathers of brown from Bill’s high forehead, locking into his yearning azure eyes. “I bet he wants you. Badly.”

Bill snuck a sizable hand across the space between them, tip of a single pinky plucking at Anne’s thigh with a note of vulnerable disbelief in his voice. “You think so?”

“Yeah…” Tone evaporating into a throaty whisper, Anne cupped Bill’s crisp jaw. “Who wouldn’t?”

Lips touched, soft and delicate as Bill gently took Anne’s waist and she threaded her fingers into his brunette tresses. They shared an alleviated sigh containing decades of want as their tongues laced, Bill’s gritty chin chafing Anne’s before they parted, breath hasty and pupils blown.

“I...I wanted to do that for a long time.” Bill murmured into their intimate bubble.

Keeping one corner of her mind on the fact that they were still in a restaurant and she needed to resist the urge to maul him, Anne nodded and smiled. “Me too. I’ve wanted you for ages.”

Squeezing her hip with a crooked grin, Bill sighed in relief. “Same here.” Awash in a heady delirium, for a moment Bill and Anne simply appreciated one another’s presence, whispered touches and quieter words as their previously unspoken desire took form.

“So would you really, um…” Bill supposed if her hand were to sneak up and higher on his leg they should probably get the check. “Really be into that? With...with me and Conan, I mean?”

“Mmm...definitely.” Nipples hardening beneath her shirt at the mere thought, not to mention how Bill’s huge hand massaged over the round curve of her ass, Anne agreed. “So hot. Do you think he’d be into it?”

Nostrils flaring, Bill hid his lips for a second and shrugged his expansive shoulders. “I guess...I really don’t know for sure…”

Voice ambrosia and words an elixir which may or may not be poisonous, neither could be certain, Anne tickled under Bill’s square chin. “Do you wanna find out?”

Breath catching, Bill’s cock twitched with need as Anne’s palm slipped between his muscular thighs. “Yeah, yeah, I do…” Edging into her touch, Bill’s slightly nasal voice cracked with anticipation as he fished out his phone. “Here, just...let...let me text him.”

Bill:  _ Hey buddy how’s it going? Sorry to bother you but do you have time to chat? Nothing wrong. Just wanted to discuss something _

Within a few minutes Bill’s phone vibrated on the table. Thankfully by this time the server brought the tab and a couple of to-go boxes, but Bill didn’t know how he would manage to hide his unfurling erection when they walked out of the restaurant.

Conan:  _ Sure, no problem. Just heading home now though. Is it okay if I call you in half an hour or so? _

Bill:  _ Sounds good. Thanks man _

Scurrying outside and doing his best to shield himself behind Anne, once they reached the car she spun and took Bill’s carved face in both hands, latching onto his lips. “Mmm…”

Bill rolled Anne back against the window, kneading her ass as his burgeoning erection prodded below her navel and he licked into her mouth. “You...you wanna get in?”

“Yeah…” Anne breathed, Bill hurriedly opening the door for her before jogging around and sliding in the driver’s seat.

As soon as they shut out the world, Bill and Anne fused to one another with a mutual moan of contentment, Anne unzipping Bill’s navy hoodie as his palm stopped short on her ribcage. 

Anne guided Bill’s big hand to her breast, nodding urgently against his pink lips. “I want you so fucking badly, Bill.”

“Fuck, me too...me too…” Bill intoned as Anne molded her fingers around his thick cock over the denim of his jeans.

A lilting groan poured from Bill as he eagerly bobbed his head, hips rising of their own volition when Anne began undoing his zipper. “Is this okay?”

“Yeah, yeah…” Bill licked his lips, blinking and looking around to make sure there weren’t any people nearby. “Fuck…”

Snugging down his jeans to release his massive cock, Anne slid up Bill’s shaft with a twisting fist as she smiled against his lips. “Mmm…”

Bill’s sizable hand splayed over her abdomen, middle finger plucking at the waistband of her leggings as the windows started to fog. “Do you want me to touch you, too?”

“Yes.” Anne breathed as she deftly tugged Bill’s cock, painfully erect and nudging into the tight circle of her fingers. “Fuck, Bill… please…” 

Wriggling beneath the restrictive material as their tongues danced, Bill moaned into Anne’s mouth when he discovered the dew adorning her supple pussy lips. Anne broke their kiss to lick her palm, reclaiming Bill’s cock and jerking vigorously until his narrow hips rocked, fingers fiddling over her imploring clit.

“Mmm... _ fuck!  _ Anne...yes...fuck...I...that’s…”

Frank Zappa blared into the panting car cabin out of nowhere and in the height of his ecstasy Bill needed a second to remember his own ringtone. 

“Fuck, that’s-that’s…” Bill left Anne’s lips briefly and swallowed. “That’s Conan. Shit...I forgot I told him to call.”

Hand continuing her ministrations, Anne arched an auburn brow, pressing a smirking kiss to Bill’s rough cheek. “Answer it…”

Taking in Anne’s mischievous expression, her twinkling green eyes, Bill fished his phone from his bunched jeans. “Okay...okay…”

Sniffing a bottle of Pinot Noir as he unwound from a day of filming, when Bill answered, Conan’s faint orange brows gathered in concern at the belabored sound of his breathing. “Hey...hey buddy, wha-what’s up?”

“Hey Bill….” Gritting his teeth as Anne rubbed a thumb into his frenulum, Bill’s crisp jawline stood out with the effort of keeping himself together and his nostrils widened, holding the phone closer to his joined ear. “Everything alright?”

“Yeah, yeah, I’m good…” Huffing greeted Conan before a needy static entered Bill’s flinty tone. “ _ So good…” _

“You sure, man? You sound a little...off.”

“Yeah, sorry, um…” Squinting his uneven eyes and shaking his head, Bill cleared his throat and tried to focus on Conan instead of Anne’s talented hand. “Sorry. Yeah, so I wanted to call because, um...well...sorry if this is weird, but...do you remember what we were talking about? When we had lunch last week?”

Conan heard a faintly whispered,  _ ‘Fuck…’ _ and pursed his thin lips in worry as the maroon liquid gurgled into his glass. “What? About the 1908 Ford and the Flintstones thing?”

A strangled chuckle. “No, no, I mean…” Bill pressed his forehead to the window in an attempt to cool off, but didn’t cease his lengthy fingers rotating over Anne’s swollen clit as she nibbled at his free connected earlobe. “About-about the threesomes. Thing. Yeah…”

“Oh right.” Sipping and smacking at the tannic taste, Conan nodded, tall frame leaned against his kitchen counter. “Yeah, what about it?”

“Well, I...my friend. I..I don’t know if...maybe we...you might’ve been joking. I’m sorry…” Bill’s left eyelid twitched as Ann began fondling his balls. “But my...my friend. She and I...well, we’ve been talking about it. If you were really interested…”

Freezing with the wine halfway to his mouth, Conan swallowed hard. “Oh…? Who’s your friend, Bill?”

“Anne. Anne Brevins. The...she was on your show once. She does a web series.”

“Wait…” Conan set his glass down and narrowed his cerulean eyes as he thought back. “Redhead? Curvy? Funny and kind of...into nerd stuff, right?”

“Yup.” Bill emitted a weak laugh as he gazed at Anne’s lust laden visage in the seat opposite. “That’s her. Oh  _ fuck… _ ”

Ticking his head to the side and raising a ginger brow at the curious noises, Conan’s reedy voice inquired with a sing-song taunt. “Hey Bill...what’s going on over there? You sound a little...busy.”

“ _ Fuck _ ...yeah, I, um…” Anne juiced the wide head of his cock ruthlessly and Bill whimpered before slapping a big hand over his mouth. “ _ Fuck _ . I’m...I’m sorry. I’m with Anne. We...went out to dinner. And got to talking. And now...we’re in the car and... _ shit...fuck _ ...things...things kind of got out of hand. I...I’m sorry, buddy. I...I shouldn’t have answered…”

Conan chuckled, deep, rumbling, and amused as his excessively long legs carried him to the couch. “Oh...that’s no problem…” Spreading out, comfortable, Conan scrunched his fingers through his orange pompadour, tongue darting over his slivered lips. “Hey...why don’t you put me on speaker phone, Bill? Hmm? It sounds like you are having too much fun over there without me.”

Listening blissfully and swirling his Pinot while Bill informed Anne of his request, when Bill’s strained voice returned, Conan discarded his glass on the coffee table. “Okay, cool. Yup. Here...here you go…”

“Hello there…” Using his humorously deep sexy tone, Conan made his orange brows dance, despite no one being around to see. “Anne, can you hear me?”

“Hi Conan!” Anne replied cheerily, bending toward where Bill affixed his phone to the dash and apparently oblivious of how her fingers continued to work his thick cock. “How are you doing? It’s so great to talk to you again.”

“You too. I’m good. But…” Chuckling, Conan wove his knees back and forth and hunkered down further on the cushions. “Not as good as Bill is right now, I imagine. Sounds to me like you’re getting our boy pretty riled up over there?”

“Mmm...yeah…” Sweeping in to dot the corner of Bill’s wide mouth with a kiss, Anne gave his huge cock a generous squeeze. “I can’t help it. He’s so sexy.”

Bobbing his head in approval, Conan’s large hand rested atop his lithe thigh as he closed his eyes. “Mmm. Yes, he is. Tell me. What are you two up to?”

“Oh, you know…” Anne responded casually over the background of Bill’s panting, trying to contain her own moan as Bill expertly flicked her clit. “Just playing with Bill’s cock in a parking lot. A regular Tuesday night. Nothing fancy…”

Conan laughed, palm to his belly and corners of his eyes crinkling. “Perfect. So...I bet Bill’s got a great cock. Am I right?”

“Oh you know it.” Tittering as she dragged her teeth over the sensitive skin of Bill’s pale neck, Bill tried to erase his flattered smile. “Long. Thick. Gorgeous.”

“Mmm...I knew it.” Stiffening beneath his jeans, Conan palmed himself over the denim and nodded. “Anne? Tell me. Do you want to suck Bill’s cock? I bet he would love it if you made him feel so good with that pretty mouth of yours.”

“Yes.” Bill and Anne responded in unison, but with drastically different inflections. Bill’s keening and desperate, Anne’s determined and eager.

Chuckling into a hum as he unbuttoned his pants, Conan crept his fingers below his boxers. “Mmm...good. Suck that cock, Anne. I know you’ll do a great job driving Bill wild over there for me.”

Kneeling on the seat before scooping her wavy scarlet tresses over one shoulder, Anne nodded. “Mmm...definitely.” Anne lowered herself to Bill’s lap, curvaceous lips enveloping the leaking tip of his substantial cock and sucking the salinic dew. 

“Oh  _ fuck… _ ” Bill gasped as Anne sank down the length of his shaft, massaging over her scalp and swallowing heavily. “Fuck…  _ yeah… _ ”

Conan stroked, mind flooding with images of Bill and Anne’s union. “Mmm...Bill. Talk to me. Tell me what she feels like. How is it?”

“So...so good…” Words puffing out as Bill nodded exuberantly, his pelvis tilted and his big hands laced into Anne’s red hair. “Fuck...so...warm...and wet...Anne, your mouth...your throat... _ fuck!” _

“Fuck…” Jerking rapidly, Conan squirmed on the cushion and bobbed his head. “Good. Bill...can..can you bring the phone closer? I want to hear. I want to hear the sound of her sucking you.”

“Yeah, yeah, just…” Lewd slurping and moaning flooded Conan’s ear and he started humping his fist. “ _ Fuck! Anne, yes! Suck me! Don’t stop!” _

“Anne? Honey, sorry to interrupt. Sorry Bill, just one quick question…”

Anne popped off at Conan’s query, wiping the drool from her lips. “Yeah?”

“Do you want to let our beautiful Bill fuck your face? Hmm? Let him cum in your throat?”

“Oh hell yes.” Pausing to comb her fingers through Bill’s brunette tendrils, Anne grinned. “He deserves to let go and feel good.”

“So true. Go right ahead, Anne.” 

Conan’s reedy command tightened Bill’s balls before Anne ensconced him once again and he let out a tortured whimper. “ _ Oh fuck...fuck…” _

“Do it, Bill.” Conan’s chest heaved as he fucked his own hand, awash in fantasy. “Fuck her mouth.  _ Hard _ .”

Huge hands taking Anne’s skull, Bill nodded urgently. “Yeah...yeah, okay…” 

Bill began timidly driving his cock into the tantalizing wet heat. Until Anne’s moans buzzed into the base of his spine, and she pulled at his wrist as she gobbled. “ _ Oh fuck! Fuck, Anne, yes!”  _

Massive cock slamming into the saliva strewn circle of her mouth, Bill braced his broad back against the seat and groaned. “ _ Fuck! Fuck, Anne! So fucking good! Your mouth! I...I...Fuck! Fuck” _

“Mmm, yeah, suck that cock…” Conan purred as he tugged himself to oblivion. “Bill? Are you playing with her pussy? Don’t leave Anne hanging, now.”

Unsure why Conan’s orders titillated him so, Bill nodded and acquiesced, slithering a large hand back inside of Anne’s leggings to locate her engorged clit. “ _ Yes, yes! I...I am...fuck!” _

“Tell me.” Pumping madly, Conan’s voice sank into a valley of erotic edict. “What’s she feel like? Make her cum, Bill. Make her scream around your cock and fuck her face.”

Bill raced between Anne’s legs as her head dribbled in his lap, his pleading cock hammering into her reverberating throat with abandon as damp smacking sounds flooded the car. “ _ So wet...s-so good...Oh...oh fuck! Conan! Anne! I’m...I’m gonna fucking cum! Fuck! Fuck!”  _

Toes curling and hanging on, voice high and vulnerable, Conan wheezed into the phone. “ _ Yes, Bill! Fuck! Cum in her throat! Finger that pussy! Don’t fucking stop! Fuck! Yes!” _

Thighs snapping shut as the quivering overtook her bent figure, Anne fought to keep her cheeks hollowed and her head moving with the same velocity as she shrieked around Bill’s sensitive flesh.

“ _ Oh fuck! Anne! Conan! Fuck! I...I...fuck! FUCK!”  _ Left eye fluttering and shelf of his shoulders collapsing, Bill folded over Anne as he shoved her head down to his root. Bill’s pelvis hopped with every thick surge of his hot cum down her hoovering throat, and Anne suckled greedily, eyes shut and nostrils open as she waited for him to finish.

“Oh...oh fuck...Anne…” 

Threads of sticky white cum decorating his PBR shirt, Conan deflated onto the couch, crystalline blue eyes blinking up at the ceiling as he gulped for air. “Mmm...nice…” Listening to Anne and Bill’s panting as he recovered, Conan replaced his softening cock before sitting up. “So...do you two want to come over tomorrow? Say...nine? This was fun and all, but...I prefer the real thing.”

Once again, Bill and Anne both responded, “Yes.”

After solidifying their plans, Bill, weary and sated, brought Anne home. Though tempted to invite him in for the night, both agreed to save their passions for the following evening. Sharing a languorous kiss, Anne made her goodbyes and Bill waited until she got inside safely before departing.

The next evening, Bill rolled up to Anne’s house sporting a blue henley and ten fingers which refused to sit still on the steering wheel. When Anne emerged in a revealing red dress paired with black heels, Bill fought the instinct to pull her into a frenzied embrace, the two pleasantly squirmy as they drove to Conan’s house.

Conan answered the door in a smart green button up, welcoming them with lanky arms and smile spread wide. “Hey, good to see you guys. Come on in.”

Anne propped up on her toes, inhaling Conan’s fresh scent as they hugged and grinning profusely when his thin lips brushed her cheek. “Hey Conan, good to see you.”

Though both physically affectionate men by nature, when Bill went in for he-didn’t-know-which hug in the years since he and Conan met, he shifted his eyes away, prepared for awkward back patting and hips a mile apart, all too aware of the unfolding situation.

But Conan’s gangly arms lassoed him in for a warm, intimate embrace, tips of his long fingers inching over the back of Bill’s collar to touch the smallest bit of bare ivory skin as he chuckled. “Mmm...good to see you, Bill.”

“You too, buddy.” 

Conan tingled at the sensation of Bill’s powerful grasp tightening around his narrow frame, indulging in a light squeeze of Bill’s love handles before they moseyed to the kitchen. “So...you two thirsty? Beer? Wine? Water?”

Both Bill and Anne shook their heads. “Nope, I’m good.”

“Hungry? I don’t cook, but…” Shrugging, Conan scrubbed through his tangerine tresses and glanced at the refrigerator. “I have some fruit. Cheese and crackers. Stuff like that.”

“I’m okay.” Anne replied and Bill agreed. “Thank you, though.”

“Alright, so…” Sharp chin dropping and eyes a cloudless sky of surprising calm, though his tall frame bounced slightly as his leg wouldn’t stop moving, Conan looked from Anne to Bill and back again. “Do you wanna go upstairs? Get started then?”

Bill imprisoned a dollop of air in his firm chest, licking his lips and folding them under as his eyes ping ponged from Conan to Anne. “Yeah, that...that sounds good.”

Anne touched Bill’s elbow in hopes of leeching some of the strain from his wide grin. “Yeah, for sure.”

“Great, come on.” Conan’s mind bogglingly long stems led them up the staircase and into his bedroom, large, airy, and tastefully appointed. Turning to Anne and Bill, Conan sighed before he began unbuttoning his shirt. “Alright, well...I haven’t done this before either, but...I imagine it’s a little bit like comedy, right? We want room to riff, but an outline might be...helpful.”

Smirking and bobbing his head in relief, Bill told his hands to stay still as Conan exposed more and more of his white undershirt. They didn’t listen. “Right. Yeah, I think that’s a good idea.”

“Same here.” Anne replied.

“Nice, so…” Tugging his shirttails free, Conan paused and sized them up. “Anything specific either of you want to do? Or not do? I’m pretty open to suggestions, I think. Anne?”

“Oh, um…” Caught off guard a bit as she contemplated removing her heels, Anne pursed her lips and mulled. “Yeah, well, I guess I’d like to cum a couple of times. How isn’t so important…”

With a close-mouthed chuckle, Conan poked Bill with a sharp elbow. “Oh, I think we can do better than that…”

Anne grinned at their smiles. So different and yet mirrored. Conan confident and direct, Bill coy and deferential. Both surrounded by chiseled features and hungry blue eyes. “Yeah, and, well...I haven’t done it, but I thought it could be hot. And…” Palm aloft, Anne apprehensively laughed. “I honestly don’t know if I’ll be able to, so...take it slow, fellas. But...maybe both of you? Would want to be inside of me? You know…” Anne looked up at them through her eyelashes as she fidgeted with the hemline of her dress. “Same entrance, same time.”

Dark eyebrows shooting up his forehead, Bill turned down the corners of his wide mouth in appraisal. “Okay...cool. We can try that.”

“Mmhmm…” Conan shrugged out of his green shirt with a smirk. “Definitely. How about you, Bill?”

“Well, um…” Bill undid an ineffectual button on his henley, cobalt eyes examining the carpet. “I’d like to go down on you, Anne. If...if you want. And yeah…” Smiling over at her, Bill let out an anxious giggle. “I want to be inside you, too. But, um…” Scrunching his toes, Bill rocked back and forth, lower lip protruding as his gaze shifted to Conan undoing his belt. “I don’t...know where you stand on…” Bill quietly pointed a finger, first to himself, then to Conan, shrugging before he cleared his throat. “So…”

Conan took in Bill’s slumped shoulders, the avoidant eyes and skittering hands, and slowly closed the distance between them, cupping Bill’s sandpaper cheek as he swiveled in. “What do you want, Bill? Hmm?” Voice low and breath hot, Conan halted an inch from Bill’s pink lips, fingers trickling through his chestnut locks. “Do you want me to fuck you?”

“Yeah…” The single syllable leaked out of Bill with an unexpected longing as he leaned forward into Conan’s touch, fisting in his white undershirt with nostrils wide. “I do.”

Conan snuck down to squeeze Bill’s tiny ass, joining their lips for a kiss. Bill didn’t know how both of his large hands ended up prancing through the orange field of Conan’s hair before they parted, blue eyes glittering and chests rising with anticipation, but he nodded enthusiastically when Conan replied, “You got it.”

“As for myself…” Stepping back, Conan stopped with his jeans unzipped and finally Bill and Anne caught up, shedding their shirt and dress respectively. “I just want to fuck you both. And, well…” The sky of Conan’s eyes landed on Anne’s exposing curves and he unconsciously licked his lips. “I think after how well you took care of Bill last night, Anne, we should really start out giving you some more...focused attention. Pretty sure Bill likes eating pussy as much as I do.” Though self conscious revealing his solid chest and little belly with their covering of fluffy dark hair, Bill nodded in agreement as he stripped down to his boxers and Anne blushed. “So if that works for everyone…” All three stood around in their underwear as if waiting for the starting gun on a race while Conan audibly exhaled. “We might as well get to it.”

Hands behind her back to reach the clasp, Anne removed her bra, going toward the bed before she lowered her black lace panties. “Alright, I’ll just…”

Conan and Bill locked eyes as their thumbs hooked into the waistband of their boxers, and both silently knew the urge to make a joke in that moment proved almost irresistible. But, simply chuckling, they dropped the fabric to the ground before joining Anne on either side of the mattress.

Erection at quarter mast as his long body stretched out beside her, Bill drew invisible patterns over Anne’s abdomen as he scanned her emerald eyes. “Anne, do you want me to go down on you?”

Squeezing her thighs together to appease her begging clit as she traced the line of Bill’s crisp jaw stubble, Anne nodded. “Yes. Please. Fuck...I’ve wanted that forever, Bill…”

“Mmm…” Shuffling down the bed and rolling Anne’s legs apart beneath his strong grasp, Bill grinned. “Me too.”

As Bill’s supple lips touched a kiss to one of her thighs, and then the other, working toward the dewy treasure ahead, Conan’s long fingers cleared the strands of scarlet from Anne’s face and his sunny smile warmed from above. “Hey Anne…”

“Hey…” Whisper lost by the time his thin lips dipped down, Anne played with the orange curlicues at the base of Conan’s neck, relishing how his large palm flowed down her neck and between her breasts, combing encouragingly through Bill’s dark hair as he breached the crest of her pussy with a moan.

“Oh...oh fuck…” Anne gasped as Bill’s sturdy jaw bound forward, long tongue whipping over her clit as Conan massaged her breasts. “Yes…”

Within minutes Anne floated on a sea of euphoria, four firm hands kneading her pale flesh as Bill lapped at her swelling clit, his cheeks scraping her thighs while Conan’s tongue spun in her mouth.

“ _ Oh fuck! Fuck!”  _ Green eyes squinching as Bill’s pink lips encased her and vehemently sucked, Anne trembled and snatched at Conan’s slender arm. “ _ Fuck! I’m gonna cum! Yes! Fuck!” _

“Mmm...fuck yeah…” Conan petted over Bill’s lapping head, tip of his long cock shining with precum as he observed Anne’s writhing body and listened to Bill moaning between her legs. “Eat that pretty pussy, Bill. Make her cum on your face.”

Revved by Conan’s words, Bill’s big hands clamped over Anne’s hips and dragged her wriggling to his sharp jaw with a snarl before redoubling his efforts. “ _ Oh FUCK!”  _ Anne looked down to see two blazing coals of blue staring up as Bill mercilessly consumed her dripping pussy, slathering his gritty cheeks with abandon. “ _ Fuck! Yes! Bill! Don’t stop! You’re making me cum so hard! Fuck! Fuck!” _

Anne’s mouth too distracted by screaming to continue kissing, Conan brushed his thin lips to her forehead before leaving the mattress. So preoccupied with his task, Bill didn’t notice Conan’s circuit until a sizable hand caressed his wide back. 

Since he lured Anne into a valley between peaks, Bill popped up, face shining and curious, turning to Conan while his fingers spun over Anne’s engorged clit. “Hey buddy…”

“Hey…” Conan stole Bill’s swollen pink lips, the unctuous taste of Anne shared between them as he kneaded Bill’s tiny asscheek. “So...can I warm you up while you’re taking care of lovely Anne here?” Azure eyes sliding from Anne, to Bill’s backside, Conan lifted a quizzical orange brow. “Taste you? Fingers, too, if you want them.”

Bill rolled his hips forward, rubbing his purple cock into the mattress as he eagerly nodded before his speech emerged a beg. “Uh huh. Yeah. Please. I want that.”

Though Conan’s mouth said, “No problem” his eyes chimed,  _ ‘Thought so’  _ before he grabbed a bottle of lube from his bedside stand and hunkered down behind Bill. 

Bill tried to maintain his focus on Anne, savoring her taste, her scent, as he coaxed her to yet another orgasm, but as Conan opened his cheeks and Bill hesitantly inched his thick thighs apart, his attention divided.

The sensation of Conan’s sharp jaw tucking between his pillowy flesh, his slippery tongue painting over the tight circle of muscle, made Bill gasp between Anne’s legs. “Mmm... _ fuck!” _

Conan swirled over Bill’s hole, laser focused on the muscles in his broad back flexing and shuddering as he rubbed a hand over their impressive surface. Popping open the bottle of lube, Conan warmed the sticky liquid before applying a dollop to Bill’s entrance. “You ready?”

“Oh fuck,  _ fuck yes! Please!” _ Voice splintered in his urgency, Bill nodded against Anne’s thigh. “ _ Now!” _

“One? Two?”

Too worried about coming off desperate to ask,  _ ‘Is three an option?’  _ Bill simply breathed. “Two. Two, please.”

Lips decorating Bill’s small cheek, Conan worked inside the tight heat, curling until he hit the spot which caused every tendon in Bill’s shapely legs to leap. “ _ Fuck!”  _

“Mmm…” Conan chucked against Bill’s fair skin as his freckled fingers tamped into his prostate. “How’s that, Bill?”

“ _ S-so good. Fuck! Fuck… _ ” Bill’s tongue lolled listlessly over Anne in his haze, but she didn’t mind, awash in a delirium of her own. “Fuck, just...please. Please touch me…”

“I am touching you, Bill…” Teasing, Conan’s teeth sank into Bill’s ass with a chuckle.

Zing of Conan’s bite paired with the internal prod of his fingertips overwhelming, Bill whipped around, growling as his huge hand closed over Conan’s wrist. “Touch my cock.”

Conan’s blue eyes iced over with challenge, nipples erect at the newfound fire and confidence uncovered in Bill’s lust-ravaged form. But Conan ripped his wiry arm away, coming to his feet and yanking Bill up by a fistful of brown hair until his connected ear lay flush to his slivered lips, breath warm and words dry. “I’ll do you one better. Get that big cock inside her right now so I can fuck your tight ass like you’ve been begging me to for years.”

Though the thought of how long Conan knew about his attraction wandered vaguely through Bill’s mind, he couldn’t waste much time on the notion, libido almost as demanding as the freckled countenance staring him down. “Fuck. Yes.”

Grinning in satisfaction, Conan patted Bill’s sandpaper cheek before tearing two condoms off from the strip in his drawer and handing one to Bill. Both men distracted with applying their prophylactics, Anne took the opportunity to drink in their beauty, comparable and yet distinct.

Both were tall, blue-eyed, and sported features a classic sculptor would strive to recreate. But where Bill received a double dose of width, Conan got the height, not to mention the hair. And though both possessed legs Anne, and, frankly, any other woman she knew would kill for; Conan’s were that of a ballerina, slender and freakishly long. Whereas Bill’s were ripped and elegant. But, Anne couldn’t deny that while both of her handsome comedy men were blessed with an abundance of gifts, their stunning endowments being just one on the list, neither could boast of a backside, and this never failed to make her smile.

Bill positioned himself atop Anne, drawing the wide head of his cock through her folds. “Are you ready?”

“Yup.” Anne draped her arms over his mountainous shoulders with a smile and parted her knees. Tilting his hips forward into Anne’s drenched heat with a groan, Bill’s eyes fluttered shut and she gasped, rolling her pelvis to accept his thick cock. “Mmm...fuck.”

Bill held still, arching back and waiting while Conan glopped more lube over his substantial cock and Bill’s hole. “Alright Bill, you good?”

“Yeah.” Crooked grin boundless, Bill nodded and reached back to give Conan’s speckled forearm a squeeze. “I’m ready.”

Conan inched inside the constrictive heat of Bill, face scrunching and mouth dropping. “Oh...oh fuck...Bill, you’re so fucking tight.  _ Yes… _ ”

Bill shivered as Conan sheathed himself to the hilt, big hands grasping Bill’s narrow hips as all three settled into a breathing, united quiet.

Then, with precision, Conan retracted before surging back into Bill’s rapacious cavity, hissing at the intoxicating pull of the paper-thin skin around his cock. “Oh Bill...fuck…your ass…”

Meeting Anne’s viridescent gaze with expressive brows knit in something resembling delicious agony, Bill took her lips and thrust. “Mmm…”

Much like comedy improvisation, it took time for the three to adjust to a desirable cadence. But once they picked up on each other’s timing, the joy flowed effortlessly beneath the stage light of their passion, Bill plowing into Anne’s sopping pussy, every stroke augmented by Conan’s hips hammering from behind.

“ _ Oh fuck! Yes! So good! Fuck me! I love your cock!” _

_ “Fuck! Fuck! You feel so fucking good! Don’t stop! Keep going!” _

A thrashing beast of twelve limbs and three screaming heads, Conan, Bill, and Anne humped hectically as the mattress shook. High forehead balanced to hers, Bill barreled inside of Anne, sandwiched between her and Conan, the prodding against his prostate and the incredible, repeated cinching of her pulsating pussy undeniable. “ _ Oh fuck! Fuck! I’m gonna cum! Gonna cum so hard! Fuck! Fuck!” _

Conan cracked a palm over Bill’s little ass, panting his way through a chuckle as he pounded his thick cock inside. “ _ Fuck yeah, Bill! Cum! Fuck her hard, Bill! Cum for me! Cum! Cum!” _

As Conan bore foreward, weighing Bill down with gleeful intent, Anne’s pussy squeezed as she shrieked. Bill morphed into a flinching being of desperation, left eye motoring as he seized between their sweating bodies, cock throbbing and whining as he clawed at the sheets.

“ _ Oh...oh fuck...I...fuck…”  _

Extricating himself so as not to overstimulate the already flinching Bill, Conan got up to throw away the condom. When he returned, Bill flopped beside Anne, built chest booming as he sucked in air and lazily cascaded a big hand past her smiling face.

“Mmm…” Conan rolled in beside Anne with another condom in hand, cupping her pallid cheek. “So...you feel up to riding me, beautiful?”

Though tired, Anne couldn’t resist and exuberantly nodded. “Definitely.”

Straddling Conan’s svelte hips, Anne lowered onto his huge cock. Conan’s strong grip tilted her forward, his skinny thighs spreading to rotate more effectively into her depths before he placed a winding thumb over her clit and their mouths met.

Bill watched as he recovered, the languid wave of Anne and Conan’s bodies, paired with their noises; Anne’s a syrup of rapture as she bounced on Conan’s substantial cock, Conan’s nasal moans puffing with purpose as he propelled his pelvis, serving to stiffen Bill before he ever thought possible.

“ _ Oh fuck! Conan, yes! Fuck! I’m gonna cum! Yes! Yes!” _ Red hair tossed back and throwing her hips furiously to and fro, Anne’s eyes rolled as waves of pleasure lit over her wan flesh and her knees jiggled in the air.

Conan hummed proudly as Anne came, rocking gently within and smiling before Bill’s lengthy fingers brushing his orange tresses startled him to the side.

“Do, um…” Bill smoothed a sizable hand down Anne’s arm and arched a prominent brow. “Did you want to try that...what you mentioned. Both of us inside now?”

“Oooh yes.” Anne stopped moving atop Conan for a minute while Bill selected a fresh condom. 

Though tricky to position themselves appropriately, Conan staying on his back and pulling out while Bill got as near as possible behind Anne, once Conan closed the tips of their cocks in his big fist, angling toward Anne’s sopping pussy with lip bitten in concentration, she merely needed to tell her body to relax and slowly, slowly accept the bewitching stretch. 

“Oh... _ oh!” _ High note entering her tone as Anne screwed up her face, Conan looked from her to Bill and back again in concern.

“Are you alright?”

“You okay? Should we stop?”

Two soft nasal voices cradled from either side and the warmth, the smile, their care imbibed expanded throughout her body, helping Anne release the muscles of her vagina and nod. “Yeah. Yeah, I’m good. Thanks. Keep going…”

Once notched within, Bill and Conan each took one of Anne’s hips, anchoring her between as Conan leisurely twiddled her clit. The sensation proved strange, but spectacular. For Anne, the nearly overwhelming stretch stung in the best of ways, and with every undulation, the head of Conan’s cock jammed into her g-spot. 

For Bill and Conan, though they were definitely inside of a slick pussy and this experience couldn’t be called novel, the feel of one another slipping past, like two gentleman out for a stroll at 2 a.m. who happen upon one another in the street and grin, tip hats, maybe wave, even though they are perfect strangers, fascinated all parties involved.

Bill’s powerful arms hooking over her shoulders and Conan leading her hips in their circuitous dance, Anne was the first to tumble off the cliffs into divinity, violently convulsing with eyes white and voice wailing. “ _ Fuck! I’m cumming! I’m cumming! So good! Fuck! Fuck!”  _

Conan folded forward, massive cock slamming into Anne with a whimper as he clutched her trembling body near. “ _ Oh fuck! Fuck! Anne! Bill! Gonna make me cum! Gonna cum so hard! Yes! Fuck!”  _

Bill took Conan’s hand, drunk on the expression contorting his freckled face as he raced within Anne’s fluttering pussy. “ _ Anne! Conan! Oh fuck! Fuck! Fuck! Yes!” _

Spring back with his cerulean eyes aflicker, Conan’s hips jumped and he squeezed Bill’s fingers in a pincer grip as he whined through his shattering orgasm. “ _ Oh fuck...Bill...Anne...fuck...fuck…” _

Broad body smushing them both down in his final moments, Bill bared his rounded teeth, nostrils gaped as he rocketed forward into the throbbing heat. “ _ I’m gonna cum! Fuck! Yes! Fuck! Fuck! I’m cumming! Fuck!” _

Bill’s tall frame hammered them both down once, twice, thrice. Groans vulnerable and hands uncoordinated, Bill deflated, and for a couple of minutes they melted together, a pile of useless, sweaty limbs.

Eventually they unraveled. Exhausted beyond measure but containing enough energy to support their smiles as Anne tucked between Conan and Bill’s long bodies, fingers exploring delicately through crevices and over hills as Conan turned out the light.

Within seconds, unable to resist his comedy instinct, Conan’s olde tyme voice broke their companionable quiet, ringing out into the darkness. “Ahoy hoy! U up?”

“Ahoy!” Bill responded without missing a beat and even in the shadows Anne covered her eyes and laughed. “New phone, who dis?”

“If this is for fornicating…” Conan chuckled, the sound of Bill’s high pitched giggles ricocheting off the walls. “Then you should say, ‘fornication plea!’”

“Ahoy hoy! Fornication plea! Fornication accepted. Forthwith!”

“My area shall meet your...area. We will touch...areas. Forthwith!”

Unsure exactly how these two dorks managed to concentrate long enough to make her cum half a dozen times or more, Anne shook her head and patted Bill and Conan’s carved cheeks before they snuggled beneath the blankets. “Ahoy.”

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom. I also accept requests!


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